On May 18, 1986, Brian Skrudland doesn’t only break Canadiens history, but National Hockey League history by scoring the quickest goal in overtime during a playoff game. It would have taken him nine seconds to beat the opponent’s netminder as the Canadiens faced off the Calgary Flames for a second time in the Cup finals. Skrudland’s quick goal would give the Habs a 3-2 win, and the necessary boost to win four straight games to finally hold the 23rd Stanley Cup.